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HRP20192197T2 - CARBAZOLE DERIVATIVES - Google Patents

CARBAZOLE DERIVATIVES Download PDF

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Publication number
HRP20192197T2
HRP20192197T2 HRP20192197TT HRP20192197T HRP20192197T2 HR P20192197 T2 HRP20192197 T2 HR P20192197T2 HR P20192197T T HRP20192197T T HR P20192197TT HR P20192197 T HRP20192197 T HR P20192197T HR P20192197 T2 HRP20192197 T2 HR P20192197T2
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Croatia
Prior art keywords
carbazole
carboxamide
fluoro
tetrahydro
hydroxypropan
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HRP20192197TT
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Croatian (hr)
Inventor
Saleem Ahmad
Douglas G Batt
Qingjie Liu
John E. Macor
Joseph A. Tino
Scott Hunter Watterson
Satheesh Kesavan NAIR
Tarun Kumar MAISHAL
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Bristol-Myers Squibb Company
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Application filed by Bristol-Myers Squibb Company filed Critical Bristol-Myers Squibb Company
Publication of HRP20192197T1 publication Critical patent/HRP20192197T1/en
Publication of HRP20192197T8 publication Critical patent/HRP20192197T8/en
Publication of HRP20192197T2 publication Critical patent/HRP20192197T2/en

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    • AHUMAN NECESSITIES
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    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445Non condensed piperidines, e.g. piperocaine
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    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Claims (18)

1. Spoj formule (I) [image] ili njegova sol, gdje: dvije isprekidane linije predstavljaju ili dvije jednostruke ili dvije dvostruke veze; i R1b i R2b su prisutni samo ako su dvije isprekidane linije dvije jednostruke veze; Q je: (i) [image] (ii) [image] [image] (iii) [image] [image] [image] ili (iv) [image] [image] [image] R1a je: (i) H, -CN, -CF3, -CH3, -CR8aR8bOH, -CR8aR8bCR8aR8bOH, -CH(OH)CH2OH, -NHR9, -C(O)NR10aR10b, -C(O)(morfolinil), -C(O)(piperazinil), ili -C(O)(metil piperazinil); ili (ii) [image] R1b, kada je prisutan, je H ili -CH3, pod uvjetom da ako R1a je H onda R1b je također H; R2a je H, F, ili Cl, pod uvjetom da ako R1a je drugačije od H onda R2a je H; R2b, kada je prisutan, je isti kao R2a; R3 je H, F, ili Cl; R4 je H, F, Cl, ili -CH3; R5a je H, F, Cl, -OCH3, ili -OCF3; R5b je H, F, Cl, -OCH3, ili -OCF3; R6a je H, -CH3 ili ciklopropil; R6c je H, -CH3 ili ciklopropil; R7a je -C(O)CH=CH(R11), -C(O)C≡CR12, ili -S(O)2CH=CH2; R7b je -C(O)CH=CH2; R7c je -C(O)CH=CH2 ili -C(O)C≡CR12; R7d je -CN, -C(O)CH=CH2, ili -C(O)C≡CR13; R7e je -CH=CH2 ili -C≡CR13; R7f je pirolidinil supstituiran sa R7c, -CH=CHC(O)(morfolinil), ili -CH=CHC(O)(pirolidinil); R8a je H ili -CH3; R8b je H ili -CH3; R9 je C1-4 alkil; R10a i R10b su nezavisno H ili -CH3; R11 je H ili -CH3; R12 je H, C1-4 alkil, ili ciklopropil; i R13 je H, C1-4 alkil, ili ciklopropil; pod uvjetima da: (a) ako Q je [image] i R7d je -CN ili -C(O)CH=CH2, onda R3 je H; i (b) ako isprekidane linije predstavljaju dvije jednostruke veze, onda: (i) Q nije [image] (ii) R11, ako je prisutan, je H; i (iii) spoj formule (I) nije: [image] 1. Compound of formula (I) [image] or its salt, where: two dashed lines represent either two single or two double bonds; both R1b and R2b are present only if the two dashed lines are two single bonds; Q is: (and) [image] (ii) [image] [image] (iii) [image] [image] [image] or (iv) [image] [image] [image] R1a is: (i) H, -CN, -CF3, -CH3, -CR8aR8bOH, -CR8aR8bCR8aR8bOH, -CH(OH)CH2OH, -NHR9, -C(O)NR10aR10b, -C(O)(morpholinyl), -C(O )(piperazinyl), or -C(O)(methyl piperazinyl); or (ii) [image] R 1b , when present, is H or -CH 3 , provided that if R 1a is H then R 1b is also H; R 2a is H, F, or Cl, provided that if R 1a is other than H then R 2a is H; R2b, when present, is the same as R2a; R 3 is H, F, or Cl; R 4 is H, F, Cl, or -CH 3 ; R5a is H, F, Cl, -OCH3, or -OCF3; R5b is H, F, Cl, -OCH3, or -OCF3; R6a is H, -CH3 or cyclopropyl; R6c is H, -CH3 or cyclopropyl; R7a is -C(O)CH=CH(R11), -C(O)C≡CR12, or -S(O)2CH=CH2; R7b is -C(O)CH=CH2; R7c is -C(O)CH=CH2 or -C(O)C≡CR12; R7d is -CN, -C(O)CH=CH2, or -C(O)C≡CR13; R7e is -CH=CH2 or -C≡CR13; R7f is pyrrolidinyl substituted with R7c, -CH=CHC(O)(morpholinyl), or -CH=CHC(O)(pyrrolidinyl); R 8a is H or -CH 3 ; R8b is H or -CH3; R 9 is C 1-4 alkyl; R10a and R10b are independently H or -CH3; R 11 is H or -CH 3 ; R 12 is H, C 1-4 alkyl, or cyclopropyl; and R 13 is H, C 1-4 alkyl, or cyclopropyl; under the conditions that: (a) if Q is [image] and R7d is -CN or -C(O)CH=CH2, then R3 is H; and (b) if the dashed lines represent two single bonds, then: (i) Q is not [image] (ii) R 11 , if present, is H; and (iii) the compound of formula (I) is not: [image] 2. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje: Q je [image] [image] [image] R1a je: (i) H, -CN, -CF3, -CH3, -CR8aR8bOH, -CH(OH)CH2OH, -NHR9, ili -C(O)NR10aR10b; ili (ii) [image] R1b, kada je prisutan, je H ili -CH3, pod uvjetom da ako R1a je H onda R1b je također H; R2a je H ili F, pod uvjetom da ako R1a je drugačije od H onda R2a je H; R2b, kada je prisutan, je isti kao R2a; R3 je H, F, ili Cl; R4 je H, F, Cl, ili -CH3; R5a je H, F, Cl, -OCH3, ili -OCF3; R5b je H, F, Cl, -OCH3, ili -OCF3; R6a je H, -CH3 ili ciklopropil; R6c je H, -CH3 ili ciklopropil; R7a je -C(O)CH=CH(R11), -C(O)C≡CR12, ili -S(O)2CH=CH2; R7b je -C(O)CH=CH2; R7c je -C(O)CH=CH2 ili -C(O)C≡CR12; R7d je -C(O)CH=CH2 ili -C(O)C≡CR13; R8a je H ili -CH3; R8b je H ili -CH3; R9 je C1-4 alkil; R10a i R10b su nezavisno H ili -CH3; R11 je H ili -CH3; R12 je H, C1-4 alkil, ili ciklopropil; i R13 je H, C1-4 alkil, ili ciklopropil; pod uvjetom da ako isprekidane linije predstavljaju dvije jednostruke veze, onda: (i) Q nije [image] (ii) R11, ako je prisutan, je H; i (iii) spoj formule (I) nije: [image] 2. The compound according to claim 1 or its salt, where: Q is [image] [image] [image] R1a is: (i) H, -CN, -CF3, -CH3, -CR8aR8bOH, -CH(OH)CH2OH, -NHR9, or -C(O)NR10aR10b; or (ii) [image] R 1b , when present, is H or -CH 3 , provided that if R 1a is H then R 1b is also H; R 2a is H or F, provided that if R 1a is other than H then R 2a is H; R2b, when present, is the same as R2a; R 3 is H, F, or Cl; R 4 is H, F, Cl, or -CH 3 ; R5a is H, F, Cl, -OCH3, or -OCF3; R5b is H, F, Cl, -OCH3, or -OCF3; R6a is H, -CH3 or cyclopropyl; R6c is H, -CH3 or cyclopropyl; R7a is -C(O)CH=CH(R11), -C(O)C≡CR12, or -S(O)2CH=CH2; R7b is -C(O)CH=CH2; R7c is -C(O)CH=CH2 or -C(O)C≡CR12; R7d is -C(O)CH=CH2 or -C(O)C≡CR13; R 8a is H or -CH 3 ; R8b is H or -CH3; R 9 is C 1-4 alkyl; R10a and R10b are independently H or -CH3; R 11 is H or -CH 3 ; R 12 is H, C 1-4 alkyl, or cyclopropyl; and R 13 is H, C 1-4 alkyl, or cyclopropyl; provided that if the dashed lines represent two single bonds, then: (i) Q is not [image] (ii) R 11 , if present, is H; and (iii) the compound of formula (I) is not: [image] 3. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje: R1a je H, -CN, -CF3, -CH3, -CR8aR8bOH, -CH(OH)CH2OH, -NHR9, ili -C(O)NR10aR10b.3. The compound according to claim 1 or its salt, where: R1a is H, -CN, -CF3, -CH3, -CR8aR8bOH, -CH(OH)CH2OH, -NHR9, or -C(O)NR10aR10b. 4. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje: R6a je H ili -CH3; R6c je H ili -CH3; R7a je -C(O)CH=CH(R11) ili -S(O)2CH=CH2; i R13 je H.4. The compound according to claim 1 or its salt, where: R6a is H or -CH3; R6c is H or -CH3; R7a is -C(O)CH=CH(R11) or -S(O)2CH=CH2; and R13 is H. 5. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, koje ima strukturu formule (Ia): [image] 5. A compound according to claim 1 or a salt thereof, which has the structure of formula (Ia): [image] 6. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, koje ima strukturu formule (Ib): [image] 6. A compound according to claim 1 or its salt, which has the structure of formula (Ib): [image] 7. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje: Q je [image] 7. The compound according to claim 1 or its salt, where: Q is [image] 8. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje: Q je [image] 8. A compound according to claim 1 or its salt, where: Q is [image] 9. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje R1a je H, -CN, -CF3, -CH3, -CR8aR8bOH, -CR8aR8bCR8aR8bOH, -CH(OH)CH2OH, -NHR9, -C(O)NR10aR10b, -C(O)(morfolinil), -C(O)(piperazinil), ili -C(O)(metil piperazinil)9. A compound according to claim 1 or a salt thereof, where R1a is H, -CN, -CF3, -CH3, -CR8aR8bOH, -CR8aR8bCR8aR8bOH, -CH(OH)CH2OH, -NHR9, -C(O)NR10aR10b, -C(O)(morpholinyl), -C(O)(piperazinyl), or -C(O)(methyl piperazinyl) 10. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje R3 je F ili Cl.10. A compound according to claim 1 or a salt thereof, where R3 is F or Cl. 11. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje R3 je F.11. A compound according to claim 1 or a salt thereof, wherein R3 is F. 12. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje je navedeno spoj: (RS)-5-(3-akrilamidofenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (1); (RS)-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(N-metilvinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (2); 5-(3-akrilamido-2-metilfenil)-2,2-dimetil-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (3); 4-(3-akrilamido-2-metilfenil)-7-(2-hidroksipropan-2-il)-9H-karbazol-1-karboksamid (4); (RS)-2-(2-hidroksipropan-2-il)-5-(3-(vinilsulfonamido) fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (5); (RS)-4-(3-akrilamido-2-metilfenil)-3-kloro-7-(2-hidroksipropan-2-il)-9H-karbazol-1-karboksamid (6); 5-(3-akrilamido-2-metilfenil)-2-(hidroksimetil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (7); (RS)-5-(3-akrilamido-2-metilfenil)-6-kloro-2-(hidroksimetil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (8); 5-(3-akrilamido-2-metilfenil)-6-kloro-2,3,4,9-tetrahidro-1H-karbazol-2,8-dikarboksamid, smjesa dijastereomera (9); (RS)-5-(3-akrilamido-2-metilfenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (10); (RS)-(E)-4-(3-(but-2-enamido)-2-metilfenil)-3-kloro-7-(2-hidroksipropan-2-il)-9H-karbazol-1-karboksamid (11); 5-(3-akrilamido-2-metilfenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (12); (RS)-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(vinilsulfonamido) fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (13); (RS)-5-(3-akrilamido-2-metilfenil)-2,3,4,9-tetrahidro-1H-karbazol-2,8-dikarboksamid (14); 4-(3-akrilamido-2-metilfenil)-7-cijano-9H-karbazol-1-karboksamid (15); (RS)-4-(3-akrilamido-2-metilfenil)-7-(1,2-dihidroksietil)-9H karbazol-1-karboksamid (16); 4-(3-akrilamido-2-metilfenil)-7-(izopropilamino)-9H-karbazol-1-karboksamid (17); (RS)-5-(3-akrilamido-2-metilfenil)-N2,N2-dimetil-2,3,4,9-tetrahidro-1H-karbazol-2,8-dikarboksamid (18); (RS)-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(N-metilakrilamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (19); (RS)-2-(hidroksimetil)-5-(2-metil-3-(N-metilakrilamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (20); (RS)-N2,N2-dimetil-5-(2-metil-3-(N-metilakrilamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-2,8-dikarboksamid (21); (2R)-6-fluoro-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(N-metilvinilsulfonamido) fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (22); (2R)-6-kloro-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(N-metilvinilsulfonamido) fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (23); (2R)-6-fluoro-2-(2-hidroksipropan-2-il)-5-(3-(N-metilvinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, jedan enantiomer (24); (2R)-6-kloro-2-(2-hidroksipropan-2-il)-5-(3-(N-metilvinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, jedan enantiomer (25); (RS)-2-(2-hidroksipropan-2-il)-5-(3-(N-metilvinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (26); 7-(2-hidroksipropan-2-il)-4-(2-metil-3-(N-metilvinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (27); 7-(2-hidroksipropan-2-il)-4-(3-(N-metilvinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (28); (RS)-3-fluoro-7-(2-hidroksipropan-2-il)-4-(2-metil-3-(vinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (29); (RS)-3-fluoro-7-(2-hidroksipropan-2-il)-4-(2-metil-3-(N-metilvinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (30); 3-fluoro-7-(2-hidroksipropan-2-il)-4-(3-(N-metilvinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (31); 7-(2-hidroksipropan-2-il)-4-(2-metil-3-(vinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (32); 7-(2-hidroksipropan-2-il)-4-(3-(vinilsulfonamido) fenil)-9H-karbazol-1-karboksamid (33); 3-fluoro-7-(2-hidroksipropan-2-il)-4-(3-(vinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (34); (RS)-2-(2-hidroksipropan-2-il)-5-(3-(N-metilakrilamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (35); (R)-6-fluoro-2-(2-hidroksipropan-2-il)-5-(3-(N-metilakrilamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (36); 7-(2-hidroksipropan-2-il)-4-(3-(N-metilakrilamido)fenil)-9H-karbazol-1-karboksamid (37); 3-fluoro-7-(2-hidroksipropan-2-il)-4-(3-(N-metilakrilamido)fenil)-9H-karbazol-1-karboksamid (38); (R)-6-kloro-2-(2-hidroksipropan-2-il)-5-(3-(N-metilakrilamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (39); (S)-2-(2-hidroksipropan-2-il)-5-(3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (40); (R)-2-(2-hidroksipropan-2-il)-5-(3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (41); (RS)-5-(2-fluoro-3-(N-metilakrilamido)fenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (42); (R)-6-fluoro-2-(2-hidroksipropan-2-il)-5-(3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (43); (2R)-6-kloro-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (44); (RS)-5-(2-fluoro-3-(N-metilvinilsulfonamido)fenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (45); (RS)-5-(2-kloro-3-(N-metilvinilsulfonamido)fenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (46); (2R)-6-fluoro-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (47); 5-(3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (48); 5-(2-metil-3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (49); (RS)-5-(3-akrilamido-4-metoksifenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (50); (RS)-5-(3-akrilamido-4-(trifluorometoksi)fenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (51); (RS)-5-(3-akrilamido-4-fluorofenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (52); (RS)-5-(3-akrilamido-2-metilfenil)-2-metil-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (53); (RS)-5-(3-akrilamido-2-metilfenil)-2-(trifluorometil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (54); 5-(3-akrilamido-2-metilfenil)-6-kloro-2-(hidroksimetil)-2-metil-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, pojedinačni racemični dijastereomeri (55 i 56); 5-(3-akrilamido-2-metilfenil)-6-kloro-N2,N2-dimetil-2,3,4,9-tetrahidro-1H-karbazol-2,8-dikarboksamid, pojedinačni racemični dijastereomeri (57 i 58); 5-(3-akrilamido-2-metilfenil)-6-kloro-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, pojedinačni racemični dijastereomeri (59 i 60); 5-(3-akrilamido-2-metilfenil)-6-kloro-2-(2-hidroksipropan-2-il)-2-metil-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, pojedinačni racemični dijastereomeri (61 i 62); (S)-5-((1-akriloilpirolidin-3-il)amino)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (63); (E)-4-(3-(but-2-enamido)-2-metilfenil)-7-(2-hidroksipropan-2-il)-9H-karbazol-1-karboksamid (64); 5-(((S)-1-akriloilpirolidin-3-il)amino)-2-(trifluorometil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (65); (S)-5-(3-akrilamidopiperidin-1-il)-3,3,6-trifluoro-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (66); (S)-4-(3-akrilamidopiperidin-1-il)-3-fluoro-9H-karbazol-1-karboksamid (69); 5-(((S)-1-propioloilpirolidin-3-il)amino)-2-(RS)-(trifluorometil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (72); (S)-5-(3-(but-2-inamido) piperidin-1-il)-3,3,6-trifluoro-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (73); (S)-3-fluoro-4-(3-(N-metilbut-2-inamido)piperidin-1-il)-9H-karbazol-1-karboksamid (74); (S)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-9H-karbazol-1-karboksamid (75); (S)-4-(3-(3-ciklopropilpropiolamido)piperidin-1-il)-3-fluoro-9H-karbazol-1-karboksamid (76); 5-(((S)-1-akriloilpirolidin-3-il)amino)-2-(trifluorometil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, pojedinačni dijastereomeri (77 i 78); 3-fluoro-4-((6-vinilpiridin-3-il)metil)-9H-karbazol-1-karboksamid (87); (RS)-4-(2-akriloilisoindolin-4-il)-3-fluoro-9H-karbazol-1-karboksamid (89); 4-(2-akriloil-1,2,3,4-tetrahidroizohinolin-7-il)-3-fluoro-9H-karbazol-1-karboksamid (90); 4-(2-akriloil-1,2,3,4-tetrahidroizohinolin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (91); 4-(1-akriloilindolin-4-il)-3-fluoro-9H-karbazol-1-karboksamid (92); 4-(1-akriloilindolin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (95); 4-(1-akriloil-1,2,5,6-tetrahidropiridin-3-il)-3-fluoro-9H-karbazol-1-karboksamid (96); (RS)-4-(1-akriloilpiperidin-3-il)-3-fluoro-9H-karbazol-1-karboksamid (97); 4-(1-akriloilpiperidin-3-il)-3-fluoro-9H-karbazol-1-karboksamid, pojedinačni enantiomeri (98 i 99); 3-fluoro-4-((2-vinilpiridin-4-il)metil)-9H-karbazol-1-karboksamid (100); 4-(1-akriloilpirolidin-3-il)-3-fluoro-9H-karbazol-1-karboksamid (112); 4-(1-akriloilpirolidin-3-il)-3-fluoro-9H-karbazol-1-karboksamid (113 i 114); cis-4-(1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (115); cis-4-(1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (116 i 117); (S)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-9H-karbazol-1-karboksamid (118); cis-4-(1-akriloiloktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (119); cis-4-(1-akriloiloktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (120 i 121); 3-fluoro-4-((2-vinilpirimidin-5-il)metil)-9H-karbazol-1-karboksamid (122); cis-4-(1-akriloilheksahidropirolo[3,4-b]pirol-5(1H)-il)-3-fluoro-9H-karbazol-1-karboksamid (123); cis-4-(1-akriloilheksahidropirolo[3,4-b]pirol-5(1H)-il)-3-fluoro-9H-karbazol-1-karboksamid (124 i 125); 4-(1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-kloro-9H-karbazol-1-karboksamid (126); 4-((4aS,7aS)-1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-kloro-9H-karbazol-1-karboksamid i 4-((4aR,7aR)-1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-kloro-9H-karbazol-1-karboksamid (127 i 128); 3-fluoro-4-((2-(prop-1-in-1-il)piridin-4-il)metil)-9H-karbazol-1-karboksamid (129); 5-((S)-3-(but-2-inamido) piperidin-1-il)-6-fluoro-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (130, 131, i 132); 4-(2-akriloilizoindolin-5-il)-3-fluoro-9H-karbazol-1-karboksamid (133); 4-(1-akriloil-2,5-dihidro-1H-pirol-3-il)-3-fluoro-9H-karbazol-1-karboksamid (134); 5-(1-akriloilpirolidin-3-il)-6-fluoro-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (135); (R)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-9H-karbazol-1-karboksamid (136); 4-(1-(but-2-inoil)heksahidropirolo[3,4-b]pirol-5(1H)-il)-3-fluoro-9H-karbazol-1-karboksamid (137); 4-(1-akriloil-1,4,5,6-tetrahidropiridin-3-il)-3-fluoro-9H-karbazol-1-karboksamid (138); 4-(7-(but-2-inoil)-2,7-diazaspiro[4.4] nonan-2-il)-3-fluoro-9H-karbazol-1-karboksamid (139); 4-(7-akriloil-2,7-diazaspiro [4.4]nonan-2-il)-3-fluoro-9H-karbazol-1-karboksamid (140); 4-(1-akriloiloktahidro-5H-pirolo[3,2-c]piridin-5-il)-3-fluoro-9H-karbazol-1-karboksamid (141); 4-(1-(but-2-inoil)oktahidro-5H-pirolo[3,2-c]piridin-5-il)-3-fluoro-9H-karbazol-1-karboksamid (142); 4-(6-akriloil-3,6-diazabiciklo[3.2.0]heptan-3-il)-3-fluoro-9H-karbazol-1-karboksamid (143); 4-(6-(but-2-inoil)-3,6-diazabiciklo[3.2.0] heptan-3-il)-3-fluoro-9H-karbazol-1-karboksamid (144); 4-(7-akriloiloktahidro-2,7-naftiridin-2(1H)-il)-3-fluoro-9H-karbazol-1-karboksamid (145); 4-(1-akriloiloktahidro-6H-pirolo[3,4-b] piridin-6-il)-3-kloro-9H-karbazol-1-karboksamid (146); 4-(1-(but-2-inoil)indolin-4-il)-3-fluoro-9H-karbazol-1-karboksamid (147); 4-(2-(but-2-inoil)-1,2,3,4-tetrahidroizohinolin-7-il)-3-fluoro-9H-karbazol-1-karboksamid (148); 4-(2-(but-2-inoil)-1,2,3,4-tetrahidroizohinolin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (149); 4-(2-(but-2-inoil)izoindolin-4-il)-3-fluoro-9H-karbazol-1-karboksamid (150); 4-(1-(but-2-inoil)indolin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (151); 3-fluoro-4-((6-vinilpirazin-2-il)metil)-9H-karbazol-1-karboksamid (152); 3-kloro-4-((6-vinilpirazin-2-il)metil)-9H-karbazol-1-karboksamid (153); 4-((6-etinilpiridin-3-il)metil)-3-fluoro-9H-karbazol-1-karboksamid (154); 3-kloro-4-((6-vinilpiridin-3-il)metil)-9H-karbazol-1-karboksamid (155); 4-((2-etinilpiridin-4-il)metil)-3-fluoro-9H-karbazol-1-karboksamid (156); 3-fluoro-4-((2-viniltiazol-5-il)metil)-9H-karbazol-1-karboksamid (157); 3-fluoro-4-((6-(prop-1-in-1-il)piridin-3-il)metil)-9H-karbazol-1-karboksamid (158); 3-fluoro-4-((5-vinilpirazin-2-il)metil)-9H-karbazol-1-karboksamid (159); 4-(1-akriloil-1,2,5,6-tetrahidropiridin-3-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (160); 4-(1-akriloilpiperidin-3-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (161 i 162); (S)-4-(3-akrilamidopiperidin-1-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (163); (S)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (164); (R)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (165); (S)-4-(3-(3-ciklopropilpropiolamido)piperidin-1-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (166); (S)-4-(3-cijanamidopiperidin-1-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (167); 4-(2-akriloilizoindolin-4-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (168); 4-(1-akriloilindolin-4-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (169); 4-(1-akriloilindolin-6-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (170); 4-(1-akriloil-1-azaspiro[4.4]nonan-7-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (171); (S)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-7-(4-metilpiperazin-1-karbonil)-9H-karbazol-1-karboksamid (172); (S)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-N7,N7-dimetil-9H-karbazol-1,7-dikarboksamid (173); 3-fluoro-N7,N7-dimetil-4-(2-vinilpiridin-4-il)-9H-karbazol-1,7-dikarboksamid (174); (S)-4-((1-cijanopirolidin-3-il)amino)-3-fluoro-N7,N7-dimetil-9H-karbazol-1,7-dikarboksamid (175); (S)-4-((1-cijanopirolidin-3-il)amino)-3-fluoro-7-(4-metilpiperazin-1-karbonil)-9H-karbazol-1-karboksamid (176); 4-(2-akriloil-1,2,3,4-tetrahidroizohinolin-5-il)-7-(morfolin-4-karbonil)-9H-karbazol-1-karboksamid (177); 4-(2-(but-2-inoil)-1,2,3,4-tetrahidroizohinolin-5-il)-7-(morfolin-4-karbonil)-9H-karbazol-1-karboksamid (178); 4-(2-cijano-1,2,3,4-tetrahidroizohinolin-5-il)-7-(morfolin-4-karbonil)-9H-karbazol-1-karboksamid (179); 4-(1-akriloilindolin-6-il)-3-fluoro-7-(2-hidroksietil)-9H-karbazol-1-karboksamid (180); 4-(1-cijanoindolin-6-il)-3-fluoro-7-(2-hidroksietil)-9H-karbazol-1-karboksamid (181); 4-(1-akriloiloktahidro-6H-pirolo[3,4-b]piridin-6-il)-6-kloro-3-fluoro-9H-karbazol-1-karboksamid (182); 4-(1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-6-kloro-3-fluoro-9H-karbazol-1-karboksamid (183); 5-(1-akriloil-1,2,5,6-tetrahidropiridin-3-il)-6-fluoro-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (184); (R)-6-fluoro-2-(2-hidroksipropan-2-il)-5-((6-vinilpiridin-3-il)metil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (185); 5-(2-akriloil-1,2,3,4-tetrahidroizohinolin-5-il)-6-fluoro-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (186 i 187); 6-fluoro-2-(2-hidroksipropan-2-il)-5-((6-(prop-1-in-1-il)piridin-3-il)metil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (188); 3-fluoro-4-(2-vinilpiridin-4-il)-9H-karbazol-1-karboksamid (189); 4-(7-(but-2-inoil)oktahidro-2,7-naftiridin-2(1H)-il)-3-fluoro-9H-karbazol-1-karboksamid (190); 4-(1-akriloil-1,2,3,6-tetrahidropiridin-4-il)-3-fluoro-9H-karbazol-1-karboksamid (191); 4-(1-(but-2-inoil)-1,2,3,6-tetrahidropiridin-4-il)-3-fluoro-9H-karbazol-1-karboksamid (192); 3-fluoro-4-(5-(N-metilakrilamido)piridin-2-il)-9H-karbazol-1-karboksamid (193); 4-((1S,4S)-2-akriloil-2-azabiciklo[2.2.1]heptan-5-il)-3-fluoro-9H-karbazol-1-karboksamid (194); 3-fluoro-4-((2-metil-6-vinilpiridin-4-il)metil)-9H-karbazol-1-karboksamid (195); 3-fluoro-4-((2-metil-6-vinilpirimidin-4-il)metil)-9H-karbazol-1-karboksamid (196); 3-fluoro-4-((4-metil-6-vinilpirimidin-2-il)metil)-9H-karbazol-1-karboksamid (197); 3-fluoro-4-((3-fluoro-2-vinilpiridin-4-il)metil)-9H-karbazol-1-karboksamid (198); 4-(3-(1-akriloilpirolidin-2-il)fenil)-3-fluoro-9H-karbazol-1-karboksamid (199); 4-(3-(1-(but-2-inoil)pirolidin-2-il)fenil)-3-fluoro-9H-karbazol-1-karboksamid (200); (E)-3-fluoro-4-(3-(3-morfolino-3-oksoprop-1-en-1-il)fenil)-9H-karbazol-1-karboksamid (201); (E)-3-fluoro-4-(3-(3-okso-3-(pirolidin-1-il)prop-1-en-1-il)fenil)-9H-karbazol-1-karboksamid (202); ili 5-(2-akriloil-1,2,3,4-tetrahidroizohinolin-5-il)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (203 i 204). 12. A compound according to claim 1 or a salt thereof, wherein the compound is: (RS)-5-(3-acrylamidophenyl)-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro- 1H-carbazole-8-carboxamide (1); (RS)-2-(2-hydroxypropan-2-yl)-5-(2-methyl-3-(N-methylvinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (2); 5-(3-acrylamido-2-methylphenyl)-2,2-dimethyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (3); 4-(3-acrylamido-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide (4); (RS)-2-(2-hydroxypropan-2-yl)-5-(3-(vinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (5); (RS)-4-(3-acrylamido-2-methylphenyl)-3-chloro-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide (6); 5-(3-acrylamido-2-methylphenyl)-2-(hydroxymethyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (7); (RS)-5-(3-acrylamido-2-methylphenyl)-6-chloro-2-(hydroxymethyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide, mixture of diastereomers (8); 5-(3-acrylamido-2-methylphenyl)-6-chloro-2,3,4,9-tetrahydro-1H-carbazole-2,8-dicarboxamide, mixture of diastereomers (9); (RS)-5-(3-acrylamido-2-methylphenyl)-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (10); (RS)-(E)-4-(3-(but-2-enamido)-2-methylphenyl)-3-chloro-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide ( 11); 5-(3-acrylamido-2-methylphenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (12); (RS)-2-(2-hydroxypropan-2-yl)-5-(2-methyl-3-(vinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (13 ); (RS)-5-(3-acrylamido-2-methylphenyl)-2,3,4,9-tetrahydro-1H-carbazole-2,8-dicarboxamide (14); 4-(3-acrylamido-2-methylphenyl)-7-cyano-9H-carbazole-1-carboxamide (15); (RS)-4-(3-acrylamido-2-methylphenyl)-7-(1,2-dihydroxyethyl)-9H carbazole-1-carboxamide (16); 4-(3-acrylamido-2-methylphenyl)-7-(isopropylamino)-9H-carbazole-1-carboxamide (17); (RS)-5-(3-acrylamido-2-methylphenyl)-N2,N2-dimethyl-2,3,4,9-tetrahydro-1H-carbazole-2,8-dicarboxamide (18); (RS)-2-(2-hydroxypropan-2-yl)-5-(2-methyl-3-(N-methylacrylamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (19); (RS)-2-(hydroxymethyl)-5-(2-methyl-3-(N-methylacrylamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (20); (RS)-N2,N2-dimethyl-5-(2-methyl-3-(N-methylacrylamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-2,8-dicarboxamide (21); (2R)-6-fluoro-2-(2-hydroxypropan-2-yl)-5-(2-methyl-3-(N-methylvinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole -8-carboxamide, mixture of diastereomers (22); (2R)-6-chloro-2-(2-hydroxypropan-2-yl)-5-(2-methyl-3-(N-methylvinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole -8-carboxamide, mixture of diastereomers (23); (2R)-6-fluoro-2-(2-hydroxypropan-2-yl)-5-(3-(N-methylvinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide , one enantiomer (24); (2R)-6-chloro-2-(2-hydroxypropan-2-yl)-5-(3-(N-methylvinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide , one enantiomer (25); (RS)-2-(2-hydroxypropan-2-yl)-5-(3-(N-methylvinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (26); 7-(2-hydroxypropan-2-yl)-4-(2-methyl-3-(N-methylvinylsulfonamido)phenyl)-9H-carbazole-1-carboxamide (27); 7-(2-hydroxypropan-2-yl)-4-(3-(N-methylvinylsulfonamido)phenyl)-9H-carbazole-1-carboxamide (28); (RS)-3-fluoro-7-(2-hydroxypropan-2-yl)-4-(2-methyl-3-(vinylsulfonamido)phenyl)-9H-carbazole-1-carboxamide (29); (RS)-3-fluoro-7-(2-hydroxypropan-2-yl)-4-(2-methyl-3-(N-methylvinylsulfonamido)phenyl)-9H-carbazole-1-carboxamide (30); 3-fluoro-7-(2-hydroxypropan-2-yl)-4-(3-(N-methylvinylsulfonamido)phenyl)-9H-carbazole-1-carboxamide (31); 7-(2-hydroxypropan-2-yl)-4-(2-methyl-3-(vinylsulfonamido)phenyl)-9H-carbazole-1-carboxamide (32); 7-(2-hydroxypropan-2-yl)-4-(3-(vinylsulfonamido)phenyl)-9H-carbazole-1-carboxamide (33); 3-fluoro-7-(2-hydroxypropan-2-yl)-4-(3-(vinylsulfonamido)phenyl)-9H-carbazole-1-carboxamide (34); (RS)-2-(2-hydroxypropan-2-yl)-5-(3-(N-methylacrylamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (35); (R)-6-fluoro-2-(2-hydroxypropan-2-yl)-5-(3-(N-methylacrylamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (36); 7-(2-hydroxypropan-2-yl)-4-(3-(N-methylacrylamido)phenyl)-9H-carbazole-1-carboxamide (37); 3-fluoro-7-(2-hydroxypropan-2-yl)-4-(3-(N-methylacrylamido)phenyl)-9H-carbazole-1-carboxamide (38); (R)-6-chloro-2-(2-hydroxypropan-2-yl)-5-(3-(N-methylacrylamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (39); (S)-2-(2-hydroxypropan-2-yl)-5-(3-(vinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (40); (R)-2-(2-hydroxypropan-2-yl)-5-(3-(vinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (41); (RS)-5-(2-fluoro-3-(N-methylacrylamido)phenyl)-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (42); (R)-6-fluoro-2-(2-hydroxypropan-2-yl)-5-(3-(vinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (43 ); (2R)-6-chloro-2-(2-hydroxypropan-2-yl)-5-(2-methyl-3-(vinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8 -carboxamide, mixture of diastereomers (44); (RS)-5-(2-fluoro-3-(N-methylvinylsulfonamido)phenyl)-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (45); (RS)-5-(2-chloro-3-(N-methylvinylsulfonamido)phenyl)-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (46); (2R)-6-fluoro-2-(2-hydroxypropan-2-yl)-5-(2-methyl-3-(vinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8 -carboxamide, mixture of diastereomers (47); 5-(3-(vinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (48); 5-(2-methyl-3-(vinylsulfonamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (49); (RS)-5-(3-acrylamido-4-methoxyphenyl)-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (50); (RS)-5-(3-acrylamido-4-(trifluoromethoxy)phenyl)-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (51 ); (RS)-5-(3-acrylamido-4-fluorophenyl)-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (52); (RS)-5-(3-acrylamido-2-methylphenyl)-2-methyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (53); (RS)-5-(3-acrylamido-2-methylphenyl)-2-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (54); 5-(3-acrylamido-2-methylphenyl)-6-chloro-2-(hydroxymethyl)-2-methyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide, individual racemic diastereomers (55 and 56); 5-(3-acrylamido-2-methylphenyl)-6-chloro-N2,N2-dimethyl-2,3,4,9-tetrahydro-1H-carbazole-2,8-dicarboxamide, individual racemic diastereomers (57 and 58) ; 5-(3-acrylamido-2-methylphenyl)-6-chloro-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide, individual racemic diastereomers ( 59 and 60); 5-(3-acrylamido-2-methylphenyl)-6-chloro-2-(2-hydroxypropan-2-yl)-2-methyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide, individual racemic diastereomers (61 and 62); (S)-5-((1-acryloylpyrrolidin-3-yl)amino)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (63); (E)-4-(3-(but-2-enamido)-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide (64); 5-(((S)-1-acryloylpyrrolidin-3-yl)amino)-2-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide, mixture of diastereomers (65); (S)-5-(3-acrylamidopiperidin-1-yl)-3,3,6-trifluoro-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (66); (S)-4-(3-acrylamidopiperidin-1-yl)-3-fluoro-9H-carbazole-1-carboxamide (69); 5-(((S)-1-propioloylpyrrolidin-3-yl)amino)-2-(RS)-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide, mixture of diastereomers ( 72); (S)-5-(3-(but-2-inamido)piperidin-1-yl)-3,3,6-trifluoro-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (73 ); (S)-3-fluoro-4-(3-(N-methylbut-2-inamido)piperidin-1-yl)-9H-carbazole-1-carboxamide (74); (S)-4-(3-(but-2-inamido)piperidin-1-yl)-3-fluoro-9H-carbazole-1-carboxamide (75); (S)-4-(3-(3-cyclopropylpropiolamido)piperidin-1-yl)-3-fluoro-9H-carbazole-1-carboxamide (76); 5-(((S)-1-acryloylpyrrolidin-3-yl)amino)-2-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide, individual diastereomers (77 and 78) ; 3-fluoro-4-((6-vinylpyridin-3-yl)methyl)-9H-carbazole-1-carboxamide (87); (RS)-4-(2-acryloylisoindolin-4-yl)-3-fluoro-9H-carbazole-1-carboxamide (89); 4-(2-acryloyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-fluoro-9H-carbazole-1-carboxamide (90); 4-(2-acryloyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-3-fluoro-9H-carbazole-1-carboxamide (91); 4-(1-acryloylindolin-4-yl)-3-fluoro-9H-carbazole-1-carboxamide (92); 4-(1-acryloylindolin-6-yl)-3-fluoro-9H-carbazole-1-carboxamide (95); 4-(1-acryloyl-1,2,5,6-tetrahydropyridin-3-yl)-3-fluoro-9H-carbazole-1-carboxamide (96); (RS)-4-(1-acryloylpiperidin-3-yl)-3-fluoro-9H-carbazole-1-carboxamide (97); 4-(1-acryloylpiperidin-3-yl)-3-fluoro-9H-carbazole-1-carboxamide, single enantiomers (98 and 99); 3-fluoro-4-((2-vinylpyridin-4-yl)methyl)-9H-carbazole-1-carboxamide (100); 4-(1-acryloylpyrrolidin-3-yl)-3-fluoro-9H-carbazole-1-carboxamide (112); 4-(1-acryloylpyrrolidin-3-yl)-3-fluoro-9H-carbazole-1-carboxamide (113 and 114); cis-4-(1-(but-2-inoyl)octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-3-fluoro-9H-carbazole-1-carboxamide (115); cis-4-(1-(but-2-inoyl)octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-3-fluoro-9H-carbazole-1-carboxamide (116 and 117); (S)-4-(3-(but-2-inamido)piperidin-1-yl)-3-fluoro-9H-carbazole-1-carboxamide (118); cis-4-(1-acryloyloctahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-3-fluoro-9H-carbazole-1-carboxamide (119); cis-4-(1-acryloyloctahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-3-fluoro-9H-carbazole-1-carboxamide (120 and 121); 3-fluoro-4-((2-vinylpyrimidin-5-yl)methyl)-9H-carbazole-1-carboxamide (122); cis-4-(1-acryloylhexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl)-3-fluoro-9H-carbazole-1-carboxamide (123); cis-4-(1-Acryloylhexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl)-3-fluoro-9H-carbazole-1-carboxamide (124 and 125); 4-(1-(but-2-inoyl)octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-3-chloro-9H-carbazole-1-carboxamide (126); 4-((4aS,7aS)-1-(but-2-inoyl)octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-3-chloro-9H-carbazole-1-carboxamide and 4 -((4aR,7aR)-1-(but-2-inoyl)octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-3-chloro-9H-carbazole-1-carboxamide (127 and 128); 3-fluoro-4-((2-(prop-1-yn-1-yl)pyridin-4-yl)methyl)-9H-carbazole-1-carboxamide (129); 5-((S)-3-(but-2-inamido)piperidin-1-yl)-6-fluoro-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H -carbazole-8-carboxamide (130, 131, and 132); 4-(2-acryloylisoindolin-5-yl)-3-fluoro-9H-carbazole-1-carboxamide (133); 4-(1-acryloyl-2,5-dihydro-1H-pyrrol-3-yl)-3-fluoro-9H-carbazole-1-carboxamide (134); 5-(1-acryloylpyrrolidin-3-yl)-6-fluoro-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (135); (R)-4-(3-(but-2-inamido)piperidin-1-yl)-3-fluoro-9H-carbazole-1-carboxamide (136); 4-(1-(but-2-inoyl)hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl)-3-fluoro-9H-carbazole-1-carboxamide (137); 4-(1-acryloyl-1,4,5,6-tetrahydropyridin-3-yl)-3-fluoro-9H-carbazole-1-carboxamide (138); 4-(7-(but-2-inoyl)-2,7-diazaspiro[4.4]nonan-2-yl)-3-fluoro-9H-carbazole-1-carboxamide (139); 4-(7-acryloyl-2,7-diazaspiro [4.4]nonan-2-yl)-3-fluoro-9H-carbazole-1-carboxamide (140); 4-(1-acryloyloctahydro-5H-pyrrolo[3,2-c]pyridin-5-yl)-3-fluoro-9H-carbazole-1-carboxamide (141); 4-(1-(but-2-inoyl)octahydro-5H-pyrrolo[3,2-c]pyridin-5-yl)-3-fluoro-9H-carbazole-1-carboxamide (142); 4-(6-acryloyl-3,6-diazabicyclo[3.2.0]heptan-3-yl)-3-fluoro-9H-carbazole-1-carboxamide (143); 4-(6-(but-2-inoyl)-3,6-diazabicyclo[3.2.0]heptan-3-yl)-3-fluoro-9H-carbazole-1-carboxamide (144); 4-(7-acryloyloctahydro-2,7-naphthyridin-2(1H)-yl)-3-fluoro-9H-carbazole-1-carboxamide (145); 4-(1-acryloyloctahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-3-chloro-9H-carbazole-1-carboxamide (146); 4-(1-(but-2-inoyl)indolin-4-yl)-3-fluoro-9H-carbazole-1-carboxamide (147); 4-(2-(but-2-inoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-fluoro-9H-carbazole-1-carboxamide (148); 4-(2-(but-2-inoyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)-3-fluoro-9H-carbazole-1-carboxamide (149); 4-(2-(but-2-inoyl)isoindolin-4-yl)-3-fluoro-9H-carbazole-1-carboxamide (150); 4-(1-(but-2-inoyl)indolin-6-yl)-3-fluoro-9H-carbazole-1-carboxamide (151); 3-fluoro-4-((6-vinylpyrazin-2-yl)methyl)-9H-carbazole-1-carboxamide (152); 3-chloro-4-((6-vinylpyrazin-2-yl)methyl)-9H-carbazole-1-carboxamide (153); 4-((6-ethynylpyridin-3-yl)methyl)-3-fluoro-9H-carbazole-1-carboxamide (154); 3-chloro-4-((6-vinylpyridin-3-yl)methyl)-9H-carbazole-1-carboxamide (155); 4-((2-ethynylpyridin-4-yl)methyl)-3-fluoro-9H-carbazole-1-carboxamide (156); 3-fluoro-4-((2-vinylthiazol-5-yl)methyl)-9H-carbazole-1-carboxamide (157); 3-fluoro-4-((6-(prop-1-yn-1-yl)pyridin-3-yl)methyl)-9H-carbazole-1-carboxamide (158); 3-fluoro-4-((5-vinylpyrazin-2-yl)methyl)-9H-carbazole-1-carboxamide (159); 4-(1-acryloyl-1,2,5,6-tetrahydropyridin-3-yl)-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide (160); 4-(1-acryloylpiperidin-3-yl)-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide (161 and 162); (S)-4-(3-acrylamidopiperidin-1-yl)-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide (163); (S)-4-(3-(but-2-inamido)piperidin-1-yl)-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide (164); (R)-4-(3-(but-2-inamido)piperidin-1-yl)-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide (165); (S)-4-(3-(3-cyclopropylpropiolamido)piperidin-1-yl)-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide (166); (S)-4-(3-cyanamidopiperidin-1-yl)-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide (167); 4-(2-acryloylisoindolin-4-yl)-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide (168); 4-(1-acryloylindolin-4-yl)-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide (169); 4-(1-acryloylindolin-6-yl)-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide (170); 4-(1-acryloyl-1-azaspiro[4.4]nonan-7-yl)-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide (171); (S)-4-(3-(but-2-inamido)piperidin-1-yl)-3-fluoro-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide (172); (S)-4-(3-(but-2-inamido)piperidin-1-yl)-3-fluoro-N7,N7-dimethyl-9H-carbazole-1,7-dicarboxamide (173); 3-fluoro-N7,N7-dimethyl-4-(2-vinylpyridin-4-yl)-9H-carbazole-1,7-dicarboxamide (174); (S)-4-((1-cyanopyrrolidin-3-yl)amino)-3-fluoro-N7,N7-dimethyl-9H-carbazole-1,7-dicarboxamide (175); (S)-4-((1-cyanopyrrolidin-3-yl)amino)-3-fluoro-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide (176); 4-(2-acryloyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-7-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide (177); 4-(2-(but-2-inoyl)-1,2,3,4-tetrahydroisoquinolin-5-yl)-7-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide (178); 4-(2-cyano-1,2,3,4-tetrahydroisoquinolin-5-yl)-7-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide (179); 4-(1-acryloylindolin-6-yl)-3-fluoro-7-(2-hydroxyethyl)-9H-carbazole-1-carboxamide (180); 4-(1-cyanoindolin-6-yl)-3-fluoro-7-(2-hydroxyethyl)-9H-carbazole-1-carboxamide (181); 4-(1-acryloyloctahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-6-chloro-3-fluoro-9H-carbazole-1-carboxamide (182); 4-(1-(but-2-inoyl)octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-6-chloro-3-fluoro-9H-carbazole-1-carboxamide (183); 5-(1-acryloyl-1,2,5,6-tetrahydropyridin-3-yl)-6-fluoro-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H- carbazole-8-carboxamide (184); (R)-6-fluoro-2-(2-hydroxypropan-2-yl)-5-((6-vinylpyridin-3-yl)methyl)-2,3,4,9-tetrahydro-1H-carbazole-8 -carboxamide (185); 5-(2-acryloyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-6-fluoro-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H- carbazole-8-carboxamide (186 and 187); 6-fluoro-2-(2-hydroxypropan-2-yl)-5-((6-(prop-1-yn-1-yl)pyridin-3-yl)methyl)-2,3,4,9- tetrahydro-1H-carbazole-8-carboxamide (188); 3-fluoro-4-(2-vinylpyridin-4-yl)-9H-carbazole-1-carboxamide (189); 4-(7-(but-2-inoyl)octahydro-2,7-naphthyridin-2(1H)-yl)-3-fluoro-9H-carbazole-1-carboxamide (190); 4-(1-acryloyl-1,2,3,6-tetrahydropyridin-4-yl)-3-fluoro-9H-carbazole-1-carboxamide (191); 4-(1-(but-2-inoyl)-1,2,3,6-tetrahydropyridin-4-yl)-3-fluoro-9H-carbazole-1-carboxamide (192); 3-Fluoro-4-(5-(N-methylacrylamido)pyridin-2-yl)-9H-carbazole-1-carboxamide (193); 4-((1S,4S)-2-acryloyl-2-azabicyclo[2.2.1]heptan-5-yl)-3-fluoro-9H-carbazole-1-carboxamide (194); 3-fluoro-4-((2-methyl-6-vinylpyridin-4-yl)methyl)-9H-carbazole-1-carboxamide (195); 3-fluoro-4-((2-methyl-6-vinylpyrimidin-4-yl)methyl)-9H-carbazole-1-carboxamide (196); 3-fluoro-4-((4-methyl-6-vinylpyrimidin-2-yl)methyl)-9H-carbazole-1-carboxamide (197); 3-fluoro-4-((3-fluoro-2-vinylpyridin-4-yl)methyl)-9H-carbazole-1-carboxamide (198); 4-(3-(1-acryloylpyrrolidin-2-yl)phenyl)-3-fluoro-9H-carbazole-1-carboxamide (199); 4-(3-(1-(but-2-inoyl)pyrrolidin-2-yl)phenyl)-3-fluoro-9H-carbazole-1-carboxamide (200); (E)-3-fluoro-4-(3-(3-morpholino-3-oxoprop-1-en-1-yl)phenyl)-9H-carbazole-1-carboxamide (201); (E)-3-fluoro-4-(3-(3-oxo-3-(pyrrolidin-1-yl)prop-1-en-1-yl)phenyl)-9H-carbazole-1-carboxamide (202) ; or 5-(2-acryloyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8 -carboxamide (203 and 204). 13. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje je navedeno spoj: (S)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-9H-karbazol-1-karboksamid.13. A compound according to claim 1 or its salt, wherein the compound is: (S)-4-(3-(but-2-inamido)piperidin-1-yl)-3-fluoro-9H-carbazole-1 -carboxamide. 14. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje je navedeno spoj: 3-fluoro-4-((2-vinilpiridin-4-il)metil)-9H-karbazol-1-karboksamid.14. A compound according to claim 1 or its salt, wherein the compound is: 3-fluoro-4-((2-vinylpyridin-4-yl)methyl)-9H-carbazole-1-carboxamide. 15. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje je navedeno spoj: cis-4-(1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-fluoro-9H-karbazol-1-karboksamid.15. A compound according to claim 1 or its salt, wherein the compound is: cis-4-(1-(but-2-inoyl)octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl) -3-fluoro-9H-carbazole-1-carboxamide. 16. Farmaceutska kompozicija koja sadrži spoj u skladu sa bilo kojim od patentnih zahtjeva 2-9 ili 13-15 i farmaceutski prihvatljiv nosač.16. A pharmaceutical composition containing a compound according to any of claims 2-9 or 13-15 and a pharmaceutically acceptable carrier. 17. Spoj u skladu sa bilo kojim od patentnih zahtjeva 9 ili 13-15, za primjenu u terapiji.17. A compound according to any of claims 9 or 13-15, for use in therapy. 18. Spoj u skladu sa bilo kojim od patentnih zahtjeva 2-9 ili 13-15 za primjenu u terapiji u liječenju autoimune bolesti ili kronične inflamatorne bolesti.18. A compound according to any one of patent claims 2-9 or 13-15 for use in therapy in the treatment of an autoimmune disease or a chronic inflammatory disease.
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